# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2115226'
loop_
_audit_author_name
_audit_author_address
'Xu Han'
;Nenu
China
;
_audit_update_record             
;
2021-10-12 deposited with the CCDC.	2021-12-09 downloaded from the CCDC.
;
_audit_creation_date             2021-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 Cl2 In N7'
_chemical_formula_sum            'C22 H14 Cl2 In N7'
_chemical_formula_weight         562.12
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1353(15)
_cell_length_b                   19.683(3)
_cell_length_c                   11.535(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.588(7)
_cell_angle_gamma                90
_cell_volume                     2070.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    244(2)
_cell_measurement_theta_max      25.127
_cell_measurement_theta_min      1.628
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.427
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28475
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.087
_diffrn_reflns_theta_max         25.087
_diffrn_reflns_theta_min         2.462
_diffrn_ambient_temperature      244.64
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3062
_reflns_number_total             3661
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.194
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.259
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3661
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.259
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.5471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0799
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
In1 In 0.36363(2) 0.13151(2) 0.70318(2) 0.02420(10) Uani 1 1 d . . . . .
Cl1 Cl 0.25176(10) 0.13748(4) 0.50366(8) 0.0382(2) Uani 1 1 d . . . . .
Cl2 Cl 0.24129(11) 0.02667(4) 0.74263(10) 0.0499(3) Uani 1 1 d . . . . .
N1 N 0.4745(3) 0.23190(12) 0.6856(2) 0.0206(5) Uani 1 1 d . . . . .
N2 N 0.2125(3) 0.21310(12) 0.7655(2) 0.0248(6) Uani 1 1 d . . . . .
N3 N 1.0151(3) 0.63532(11) 0.6164(2) 0.0237(6) Uani 1 1 d . . . . .
N4 N 0.5894(3) 0.11228(12) 0.6334(2) 0.0252(6) Uani 1 1 d . . . . .
N5 N 1.0434(3) 0.69129(13) 0.5554(3) 0.0321(7) Uani 1 1 d . . . . .
N6 N 0.9439(4) 0.69749(14) 0.4718(3) 0.0403(8) Uani 1 1 d . . . . .
N7 N 0.8448(4) 0.64605(15) 0.4767(3) 0.0410(8) Uani 1 1 d . . . . .
C1 C 0.4057(3) 0.28843(14) 0.7158(3) 0.0224(7) Uani 1 1 d . . . . .
C2 C 0.6105(4) 0.35592(14) 0.6648(3) 0.0256(7) Uani 1 1 d . . . . .
C3 C 0.4706(4) 0.35130(15) 0.7058(3) 0.0283(7) Uani 1 1 d . . . . .
H3 H 0.420679 0.390804 0.726517 0.034 Uiso 1 1 calc R . . . .
C4 C 0.2579(3) 0.27741(15) 0.7612(3) 0.0221(7) Uani 1 1 d . . . . .
C5 C 0.6828(3) 0.42256(15) 0.6476(3) 0.0271(7) Uani 1 1 d . . . . .
C6 C 0.8350(4) 0.42694(15) 0.6484(3) 0.0306(8) Uani 1 1 d . . . . .
H6 H 0.891997 0.387904 0.664586 0.037 Uiso 1 1 calc R . . . .
C7 C 0.6109(3) 0.23436(14) 0.6495(3) 0.0217(7) Uani 1 1 d . . . . .
C8 C 0.1730(4) 0.32993(17) 0.7986(3) 0.0300(8) Uani 1 1 d . . . . .
H8 H 0.204759 0.375179 0.793352 0.036 Uiso 1 1 calc R . . . .
C9 C 0.6812(3) 0.29540(15) 0.6371(3) 0.0257(7) Uani 1 1 d . . . . .
H9 H 0.776203 0.296556 0.610269 0.031 Uiso 1 1 calc R . . . .
C10 C 0.9037(4) 0.48739(15) 0.6260(3) 0.0301(8) Uani 1 1 d . . . . .
H10 H 1.006596 0.489412 0.628192 0.036 Uiso 1 1 calc R . . . .
C11 C 0.0406(4) 0.31497(18) 0.8437(3) 0.0363(9) Uani 1 1 d . . . . .
H11 H -0.018059 0.350164 0.870574 0.044 Uiso 1 1 calc R . . . .
C12 C 0.6759(3) 0.16734(15) 0.6216(3) 0.0224(7) Uani 1 1 d . . . . .
C13 C 0.0826(4) 0.19891(18) 0.8090(3) 0.0333(8) Uani 1 1 d . . . . .
H13 H 0.051456 0.153454 0.811671 0.040 Uiso 1 1 calc R . . . .
C14 C 0.6021(4) 0.48080(15) 0.6252(3) 0.0342(8) Uani 1 1 d . . . . .
H14 H 0.499382 0.479154 0.626513 0.041 Uiso 1 1 calc R . . . .
C15 C 0.8210(3) 0.54565(15) 0.6000(3) 0.0266(7) Uani 1 1 d . . . . .
C16 C -0.0057(4) 0.24898(19) 0.8495(3) 0.0384(9) Uani 1 1 d . . . . .
H16 H -0.095650 0.238190 0.880360 0.046 Uiso 1 1 calc R . . . .
C17 C 0.8170(4) 0.16046(17) 0.5852(3) 0.0314(8) Uani 1 1 d . . . . .
H17 H 0.876741 0.198946 0.578215 0.038 Uiso 1 1 calc R . . . .
C18 C 0.8924(4) 0.60895(16) 0.5675(3) 0.0271(7) Uani 1 1 d . . . . .
C19 C 0.6695(4) 0.54165(16) 0.6007(3) 0.0351(8) Uani 1 1 d . . . . .
H19 H 0.612171 0.580556 0.584423 0.042 Uiso 1 1 calc R . . . .
C20 C 0.6405(4) 0.05112(16) 0.6061(3) 0.0330(8) Uani 1 1 d . . . . .
H20 H 0.578742 0.013233 0.611726 0.040 Uiso 1 1 calc R . . . .
C21 C 0.7802(4) 0.04110(17) 0.5699(3) 0.0401(9) Uani 1 1 d . . . . .
H21 H 0.813739 -0.002682 0.552687 0.048 Uiso 1 1 calc R . . . .
C22 C 0.8689(4) 0.09718(18) 0.5597(3) 0.0403(9) Uani 1 1 d . . . . .
H22 H 0.964559 0.092058 0.535249 0.048 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
In1 Cl1 2.4618(11) . ?
In1 Cl2 2.4038(9) . ?
In1 N1 2.236(2) . ?
In1 N2 2.265(2) . ?
In1 N3 2.297(3) 2_646 ?
In1 N4 2.292(3) . ?
N1 C1 1.335(4) . ?
N1 C7 1.339(4) . ?
N2 C4 1.334(4) . ?
N2 C13 1.345(4) . ?
N3 In1 2.297(3) 2_656 ?
N3 N5 1.341(3) . ?
N3 C18 1.329(4) . ?
N4 C12 1.353(4) . ?
N4 C20 1.336(4) . ?
N5 N6 1.289(4) . ?
N6 N7 1.362(4) . ?
N7 C18 1.327(5) . ?
C1 C3 1.380(4) . ?
C1 C4 1.495(4) . ?
C2 C3 1.393(4) . ?
C2 C5 1.487(4) . ?
C2 C9 1.401(4) . ?
C4 C8 1.377(4) . ?
C5 C6 1.393(4) . ?
C5 C14 1.379(4) . ?
C6 C10 1.377(4) . ?
C7 C9 1.374(4) . ?
C7 C12 1.490(4) . ?
C8 C11 1.378(4) . ?
C10 C15 1.395(4) . ?
C11 C16 1.369(5) . ?
C12 C17 1.387(4) . ?
C13 C16 1.374(5) . ?
C14 C19 1.384(4) . ?
C15 C18 1.466(4) . ?
C15 C19 1.387(5) . ?
C17 C22 1.371(5) . ?
C20 C21 1.381(5) . ?
C21 C22 1.379(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 In1 Cl1 92.71(4) . . ?
N1 In1 Cl1 92.13(7) . . ?
N1 In1 Cl2 174.08(7) . . ?
N1 In1 N2 71.99(8) . . ?
N1 In1 N3 81.81(9) . 2_646 ?
N1 In1 N4 72.02(9) . . ?
N2 In1 Cl1 92.14(7) . . ?
N2 In1 Cl2 104.40(7) . . ?
N2 In1 N3 87.61(9) . 2_646 ?
N2 In1 N4 143.98(9) . . ?
N3 In1 Cl1 173.70(6) 2_646 . ?
N3 In1 Cl2 93.45(7) 2_646 . ?
N4 In1 Cl1 90.56(8) . . ?
N4 In1 Cl2 111.34(7) . . ?
N4 In1 N3 85.97(10) . 2_646 ?
C1 N1 In1 119.31(18) . . ?
C1 N1 C7 120.9(2) . . ?
C7 N1 In1 119.73(19) . . ?
C4 N2 In1 117.64(19) . . ?
C4 N2 C13 119.6(3) . . ?
C13 N2 In1 122.7(2) . . ?
N5 N3 In1 113.8(2) . 2_656 ?
C18 N3 In1 135.9(2) . 2_656 ?
C18 N3 N5 106.5(3) . . ?
C12 N4 In1 116.57(19) . . ?
C20 N4 In1 124.6(2) . . ?
C20 N4 C12 118.8(3) . . ?
N6 N5 N3 108.7(3) . . ?
N5 N6 N7 109.7(3) . . ?
C18 N7 N6 104.9(3) . . ?
N1 C1 C3 120.9(3) . . ?
N1 C1 C4 114.9(2) . . ?
C3 C1 C4 124.2(3) . . ?
C3 C2 C5 121.8(3) . . ?
C3 C2 C9 117.9(3) . . ?
C9 C2 C5 120.3(3) . . ?
C1 C3 C2 119.7(3) . . ?
N2 C4 C1 116.1(2) . . ?
N2 C4 C8 121.2(3) . . ?
C8 C4 C1 122.7(3) . . ?
C6 C5 C2 120.3(3) . . ?
C14 C5 C2 121.5(3) . . ?
C14 C5 C6 118.1(3) . . ?
C10 C6 C5 121.2(3) . . ?
N1 C7 C9 120.9(3) . . ?
N1 C7 C12 115.2(2) . . ?
C9 C7 C12 123.8(3) . . ?
C4 C8 C11 118.9(3) . . ?
C7 C9 C2 119.7(3) . . ?
C6 C10 C15 120.3(3) . . ?
C16 C11 C8 120.1(3) . . ?
N4 C12 C7 116.4(3) . . ?
N4 C12 C17 120.8(3) . . ?
C17 C12 C7 122.8(3) . . ?
N2 C13 C16 121.9(3) . . ?
C5 C14 C19 121.2(3) . . ?
C10 C15 C18 120.7(3) . . ?
C19 C15 C10 118.6(3) . . ?
C19 C15 C18 120.7(3) . . ?
C11 C16 C13 118.3(3) . . ?
C22 C17 C12 119.6(3) . . ?
N3 C18 C15 126.9(3) . . ?
N7 C18 N3 110.2(3) . . ?
N7 C18 C15 122.7(3) . . ?
C14 C19 C15 120.5(3) . . ?
N4 C20 C21 122.9(3) . . ?
C22 C21 C20 118.1(3) . . ?
C17 C22 C21 119.7(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
